The men’s draw at Wimbledon produced some tantalizing first rounders, several of them involving some of the biggest names in the game. Here are five first-round men’s matches to keep an eye on:

[2] Daniil Medvedev (RUS) vs Jan-Lennard Struff (GER) [Medvedev leads 3-1]

Medvedev may have won the pair’s first three tour-level meetings, but in Halle two weeks ago—in their first meeting in almost two years—it was Struff who came out on top. Struff beat the Russian in the first round of the ATP 500 grass-court event, rallying from 5-2 down in the first set to win, 7-6 (6), 6-3.

“This is the biggest win—rankings wise—of my career, and to do it here on home soil is very special. I live only an hour from here,” Struff told ATPTour.com after the win, his first over a Top 2 player.

It was the 6’ 4” German’s second Top 10 win in two weeks—he had also taken out No. 7 Andrey Rublev, one of the hottest players of the clay-court lead-up season, in the first round of Roland Garros.

Can Struff’s powerful, explosive game give Medvedev the same trouble it gave him in Halle?

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[3] Stefanos Tsitsipas (GER) vs Frances Tiafoe (USA) [Tsitsipas leads 1-0]

After falling just short of winning his first major at Roland Garros, Tsitsipas was excited to switch to grass. “I’m going to try and adapt my game to this surface,” he said. “I think I have the game to play well on grass, too. I just need to be open-minded and adapt my game to this new, exciting surface.”

Based on his results, playing on grass comes naturally to him—Wimbledon was actually the first one of the four majors he reached the second week at, making it to the fourth round as a 19-year-old in 2018 before running into John Isner (and 22 aces). He fell first round in 2019 though, and now, after the 2020 event was cancelled, he’ll take on Tiafoe to get back on the winning track at SW19.

Tsitsipas won their only previous tour-level meeting, but it was a different format at the 2018 Next Gen ATP Finals—he won, 4-3, 4-3, 4-2. Tiafoe has been playing great on grass this year, too, winning a Challenger in Nottingham and reaching the quarters of Queen’s Club last week. He has three career Top 10 wins, too, including one at a major (Kevin Anderson at the 2019 Australian Open).

Tsitsipas enters his meeting with Tiafoe at a career-high No. 4 in the ATP rankings.

Tsitsipas enters his meeting with Tiafoe at a career-high No. 4 in the ATP rankings.

[24] Nikoloz Basilashvili (GEO) vs [WC] Andy Murray (GBR) [First Meeting]

Along with Novak Djokovic and Roger Federer, Murray is one of only three former Wimbledon champions in the men’s draw, winning it twice in 2013 and 2016. A wild card this year, he’ll kick off his campaign for his third Wimbledon crown against the 24th-seeded Basilashvili. The Georgian has never been past the third round at the All England Club, but he’s fresh off reaching an ATP 500 semifinal on this surface after coming through qualifying in Halle.

Murray has lost his last five matches against Top 30 players since beating Alexander Zverev at the Western & Southern Open the week before the US Open last summer. He’s also looking for his first Top 30 win at a Grand Slam since his hip injury woes began in 2017, going 0-3 against them since.

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[21] Ugo Humbert (FRA) vs Nick Kyrgios (AUS) [Tied 1-1]

In a first-round draw that was unfortunate for both players, Humbert will take on former No. 13 Kyrgios. Both men are very dangerous on grass: Humbert just won the biggest title of his career at the grass-court event in Halle, while Kyrgios reached his first Grand Slam quarterfinal here as a teenager in 2014, pulling off a stunning upset of then-No. 1 Rafael Nadal along the way.

Their last meeting was also one of the most exciting matches of the year so far, with Kyrgios rallying from two-sets-to-one down—and staving off two match points in the fourth set—to survive the Frenchman in the second round of the Australian Open in February, 5-7, 6-4, 3-6, 7-6 (2), 6-4.

If Kyrgios vs. Humbert is anything like the pair's Melbourne matchup, fans are in for a real treat.

If Kyrgios vs. Humbert is anything like the pair's Melbourne matchup, fans are in for a real treat.

[15] Alex de Minaur (AUS) vs Sebastian Korda (USA) [First Meeting]

De Minaur is more than comfortable on grass—he’s 7-2 on the surface this year (as he takes the court against Lorenzo Sonego in the Eastbourne) and just reached his first ATP final on grass in Eastbourne, not dropping a set along the way.

But going up against the 6’ 5” Korda could prove troublesome. Having recorded his first two Top 20 wins in Miami earlier this year, against No. 17 Fabio Fognini and No. 9 Diego Schwartzman, the big-hitting American took out No. 10 Roberto Bautista Agut in Halle last week for his third career Top 20 win (and first on grass). He’ll also have nothing to lose, as this is his first time playing at Wimbledon.